生物発光分子系を基盤とする機能性色素化学 : イミダゾピラジノンπ電子系の基礎化学と応用 Functional Dye Chemistry Based on Bioluminescence-related Molecules : Fundamental Chemistry and Application of the Imidazopyrazinone π-System

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著者

    • 平野 誉 HIRANO Takashi
    • 電気通信大学電気通信学部量子・物質工学科 Department of Applied Physics and Chemistry, The University of Electro-Communications

抄録

The imidazo [1, 2-<I>a</I>] pyrazin-3 (7<I>H</I>) -one (imidazopyrazinone) ring is a core structure of the luminescent substrates isolated from marine bioluminescent organisms, such as the crustacean <I>Vargula</I> (<I>Cypridina</I>) and the jellyfish <I>Aequorea</I>. To develop the bioluminescence chemistry, we revealed the unique π-electronic character of the imidazopyrazinone ring system on the basis of the pioneering study by Goto et al. In this article, we provide an overview of the fundamental chemistry of imidazopyrazinone including the molecular structure, aromaticity of the π-system, molecular orbital, solvatochromism, acid-base behavior, tautomerism, and electron-donating ability. Especially, the imidazopyrazinone π-system having a twitterionic character is sensitively affected by a microenvironment around molecules, to show a continuous absorption-spectral change. Therefore, imidazopyrazinones are useful as functional dyes to indicate a magnitude of an interaction with a microenvironment, such as a hydrogen bond and a Lewis acid-base interaction. We also describe applications of imidazopyrazinone derivatives as indicators for naked eye detection of the hydrogen-bond donor strength of a solvent molecule, the Lewis acidity of a metal ion, and a hydrophobic interaction with a protein.

収録刊行物

  • 有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN  

    有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN 64(10), 1062-1072, 2006-10-01 

    The Society of Synthetic Organic Chemistry, Japan

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各種コード

  • NII論文ID(NAID)
    10018311691
  • NII書誌ID(NCID)
    AN0024521X
  • 本文言語コード
    JPN
  • 資料種別
    ART
  • ISSN
    00379980
  • NDL 記事登録ID
    8536483
  • NDL 雑誌分類
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL 請求記号
    Z17-256
  • データ提供元
    CJP書誌  NDL  J-STAGE 
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